Diethyl Ether → Ethyl 1-carbamothioylpiperidine-4-carboxylate

9-Fluorenylmethoxycarbonyl isothiocyanate (5.90 g, 21.0 mmol) was dissolved in chloroform (20 ml) and a chloroform (10 ml) solution of piperidine-4-carboxylic acid ethyl ester (3.30 g, 21.0 mmol) was added and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated in vacuo, and the residue obtained by adding diethyl ether was collected by filtration. This was dissolved in N,N-dimethylformamide (20 ml) and piperidine (20 ml) was added and the mixture was stirred at room temperature for 1 hour. After the reaction solution was washed with ethyl acetate and the organic layer was washed with a saturated bline and dried over sodium sulfate, the residue obtained by vacuum concentration was purified by silica gel chromatography (n-hexane:ethyl acetate), and the title compound (4.34 g, 100%) was obtained.

1. concentrationThe reaction solution was concentrated in vacuo
2. customthe residue obtained
3. filtrationwas collected by filtration
4. dissolutionThis was dissolved in N,N-dimethylformamide (20 ml)
5. additionpiperidine (20 ml) was added
6. stirringthe mixture was stirred at room temperature for 1 hour
7. washAfter the reaction solution was washed with ethyl acetate
8. washthe organic layer was washed with a saturated bline
9. dry with materialdried over sodium sulfate
10. customthe residue obtained by vacuum concentration
11. customwas purified by silica gel chromatography (n-hexane:ethyl acetate)

ORD record

ord-73617e8d9c144308b825446b6c89e702

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803801B2